Dichloromethane → HCID 86723578, compound

Participants

Reaction Steps

A mixture of 4-bromo-5-methylisoxazol-3-amine (18, 0.35 g, 2 mmol), (6-methoxypyridin-3-yl)boronic acid (0.46 g, 1.5 equiv.), PdCl2dppf.CH2Cl2 (146 mg, 0.1 equiv) and Cs2CO3 (1.3 g, 2 equiv.) in aqueous DME (6 mL mixed with 0.5 mL H2O) was stirred at 100° C. for 5 h. The reaction mixture was allowed to cool to room temperature and filtered through a layer of Celite. The filtrate was concentrated and purified by chromatography (silica gel, 0-50% EtOAc in hexanes) to afford 19 (93 mg, 23%) as an off-white solid: 1H NMR (300 MHz, DMSO-d6) δ 8.15 (dd, J=0.6, 2.4 Hz, 1H), 7.69 (dd, J=2.4, 8.7 Hz, 1H), 6.90 (dd, J=0.6, 8.4 Hz, 1H), 5.41 (s, 2H), 3.88 (s, 3H), 2.25 (s, 3H). ESI MS m/z 206 [M+H]+.

Provenance & Evidence